12,13(E)-didehydro-13,14-dihydro-PGD1 compounds

ABSTRACT

Prostaglandin analogs with the following cyclopentane ring structure: ##STR1## are disclosed along with intermediates useful in their preparation and process for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins, particularly and especially as blood platelet aggregation inhibitors.

The present application is a divisional application of Ser. No. 614,244,filed Sept. 17, 1975, now pending. U.S. Ser. No. 809,248, filed June 23,1977, and also a divisional application of Ser. No. 614,244, has nowissued as U.S. Pat. No. 4,099,014.

The present invention relates to prostaglandin analogs, for which theessential material constituting disclosure therefor is incorporated byreference here from U.S. Pat. No. 4,099,014.

I claim:
 1. A prostaglandin analog of the formula ##STR2## wherein m isone to 5, inclusive; WHEREIN M₁ is ##STR3## wherein R₅ and R₆ arehydrogen or methyl, with the proviso that one of R₅ and R₆ is methylonly when the other is hydrogen;Wherein L₁ is ##STR4## or a mixture of##STR5## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being thesame or different, with the proviso that one of R₃ and R₄ is fluoro onlywhen the other is hydrogen or fluoro; Wherein R₁ is hydrogen, alkyl ofone to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms,inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenylsubstituted with one, two, or three chloro or alkyl of one to 3 carbonatoms, inclusive, or a pharmacologically acceptable cation; and WhereinZ₆ is(1) --(CH₂)₃ --(CH₂)_(g) --CF₂ -- or (2) --(CH₂)₃ --(CH₂)_(g) --CH₂--, wherein g is one, 2, or
 3. 2. A compound according to claim 1,wherein M₁ is ##STR6##
 3. A compound according to claim 1, wherein M₁ is##STR7##
 4. A compound according to claim 3, wherein m is
 3. 5. Acompound according to claim 4, wherein Z₆ is

    --(CH.sub.2).sub.3 --(CH.sub.2).sub.g --CH.sub.2 --.


6. a compound according to claim 5, wherein g is
 3. 7. A compoundaccording to claim 5, wherein g is one.
 8. A compound according to claim7, wherein R₅ and R₆ are both hydrogen.
 9. A compound according to claim8, wherein R₃ and R₄ are both hydrogen. 10.13,14-Dihydro-12,13(E)-didehydro-PGD₁, a compound according to claim 9.11. A compound according to claim 8, wherein R₃ and R₄ are both fluoro.12. 16,16-Difluoro-13,14-dihydro-12,13(E)-didehydro-PGD₁, a compoundaccording to claim
 11. 13. A compound according to claim 4, wherein Z₆is

    --(CH.sub.2).sub.3 --(CH.sub.2).sub.g --CF.sub.2 --.


14. a compound according to claim 13, wherein g is
 3. 15. A compoundaccording to claim 14, wherein R₅ and R₆ are both hydrogen.
 16. Acompound according to claim 15, wherein R₃ and R₄ are both hydrogen. 17.2a,2b-Dihomo-2,2-difluoro-13,14-dihydro-12,13(E)-didehydro-PGD₁, acompound according to claim
 15. 18. A compound according to claim 15,wherein R₃ and R₄ are both fluoro. 19.2a,2b-Dihomo-2,2,16,16-tetrafluoro-13,14-dihydro-12,13(E)-didehydro-PGD₁,a compound according to claim
 17. 20. A compound according to claim 13,wherein g is one.
 21. A compound according to claim 20, wherein R₅ andR₆ are both hydrogen.
 22. A compound according to claim 21, wherein R₃and R₄ are both hydrogen. 23.2,2-Difluoro-13,14-dihydro-12,13(E)-didehydro-PGD₁, a compound accordingto claim
 22. 24. A compound according to claim 21, wherein R₃ and R₄ areboth fluoro. 25.2,2,16,16-Tetrafluoro-13,14-dihydro-12,13(E)-didehydro-PGD₁, a compoundaccording to claim 24.